Hexabromocyclododecane
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| Names | |
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IUPAC name
1,2,5,6,9,10-Hexabromocyclododecane
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| Other names
Hexabromocyclododecane
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| Identifiers | |
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3D model (Jmol)
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| Abbreviations | HBCDD HBCD |
| ChEBI | |
| ECHA InfoCard | 100.042.848 |
| UNII | |
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| Properties | |
| C12H18Br6 | |
| Molar mass | 641.7 g/mol |
| Melting point | 186 °C (367 °F; 459 K) (175–195 °C, depending upon isomer) |
| 3.4 µg/L in water | |
| Hazards | |
| GHS pictograms | H361 and H362 |
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EU classification (DSD)
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SVHC |
| NFPA 704 | |
| [[|Supplementary data page]] | |
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Refractive index (n), Dielectric constant (εr), etc. |
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Thermodynamic
data |
Phase behaviour solid–liquid–gas |
| UV, IR, NMR, MS | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Hexabromocyclododecane (HBCD or HBCDD) is a brominated flame retardant. It consists of twelve carbon, eighteen hydrogen, and six bromine atoms tied to the ring. Its primary application is in extruded (XPS) and expanded (EPS) polystyrene foam that is used as thermal insulation in the building industry. Other uses are upholstered furniture, automobile interior textiles, car cushions and insulation blocks in trucks, packaging material, video cassette recorder housing and electric and electronic equipment. According to UNEP, “HBCD is produced in China, Europe, Japan, and the USA. The known current annual production is approximately 28,000 tonnes per year. The main share of the market volume is used in Europe and China” (figures from 2009/2010).
HBCD's toxicity and its harm to the environment are currently discussed. HBCD can be found in environmental samples such as birds, mammals, fish and other aquatic organisms as well as soil and sediment. On this basis, on 28 October 2008 the European Chemicals Agency decided to include HBCD in the SVHC list, Substances of Very High Concern, within the Registration, Evaluation, Authorisation and Restriction of Chemicals framework. On 18 February 2011, HBCD was listed in the Annex XIV of REACH and hence is subject to Authorisation. HBCD can be used until the so-called “sunset date” (21 August 2015). After that date, only authorised applications will be allowed in the EU. HBCD has been found widely present in biological samples from remote areas and supporting evidences for its classification as Persistent, Bioaccumulative and Toxic (PBT) and undergoes long-range environmental transportation. In July 2012, an EU harmonised classification and labelling for HBCD entered into force. HBCD has been classified as a category 2 for reproductive toxicity. Since August 2010 hexabromocyclododecanes are included in the EPA's List of Chemicals of Concern. On May 2013 the Stockholm Convention on Persistent Organic Pollutants (POPs) decided to include HBCD in the Convention’s Annex A for elimination, with specific exemptions for expanded and extruded polystyrene in buildings needed to give countries time to phase-in safer substitutes. HBCD is listed for elimination, but with a specific exemption for expanded polystyrene (EPS) and extruded polystyrene (XPS) in buildings. Countries may choose to use this exemption for up to five years after the request for exemption is submitted. Japan was the first country to implement a ban on the import and production of HBCD effective in May 2014.
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